Amino acids have been widely used as cosmetic raw materials as materials excellent in biocompatibility and environmental compatibility, and many attempts at derivatization have been made with aiming at further functionalization. Among major amino acids, arginine has a guanidinyl group as a characteristic functional group in the molecule and is excellent in absorbability to the skin and hair, so that various arginine derivatives have been developed. For example, Patent Document 1 reports a higher alkyl (12 to 22 carbon atoms) ester salt of N-long chain acyl (8 to 22 carbon atoms) arginine and a hair cosmetic containing the same.
Moreover, Patent Document 2 reports an N-long chain (4 to 30 carbon atoms) alkylamino acid derivative characterized by reacting 1,2-epoxyalkane having 4 to 30 carbon atoms with an alkaline metal salt or an amino acid whose carboxyl group is protected through esterification, in an alcohol or a mixed solvent of an alcohol and water.
However, the arginine derivative or N-long chain (4 to 30 carbon atoms) alkylamino acid derivative is a surfactant and may sometimes generate a tense feeling and a rough feeling, so that the amount thereof to be added to cosmetics is limited.
On the other hand, Patent Document 3 reports an arginine N-glyceryl derivative (N-(2,3-dihydroxypropyl)-L-arginine) obtained by reacting arginine with glycidol or 3-halo-1,2-propanediol. However, the arginine N-glyceryl derivative has a high moisturizing property as compared with arginine and does not generate a tense feeling and a rough feeling, but it is not sufficiently satisfactory from the viewpoints of compatibility with the skin and hair, softening of the skin, and a skin conditioning effect.
Furthermore, from the viewpoint of a production method, since a large amount of an organic solvent is required for solubilizing an acyl halide compound having 8 to 22 carbon atoms or a higher alcohol having 12 to 22 carbon atoms in the production process of Patent Document 1 and a 1,2-epoxyalkane having 4 to 30 carbon atoms in the production process of Patent Document 2 at the reaction, environmental burden is large and there is a concern about a residual solvent in the case of the use as a cosmetic base material. In the production process of Patent Document 3, for activating the α-amino group of the amino acid, pH is adjusted to 8 to 11 with an alkali agent or an acid agent. However, in the case where the amino acid and glycidol or 3-halo-1,2-propanediol are reacted in the presence of an alkali metal or the like, impurity in association with side reactions are generated, so that deterioration of a use feeling by the influence of the impurities is a problem in the case of the use as cosmetics.